CRITICAL ISSUES: Rosenberg admits under prodding that the new Drop Dead Air may be pretty good.

It seems appropriate that a piece of rock history should materialize while Rosenberg discusses his new Drop Dead Air (on his own Red Rose label), because pieces of rock history also turn up throughout the album. As a proud fan of ’60s and ’70s pop — and a proud cynic about whatever’s currently on the charts — Rosenberg’s not shy about referring to the music he loves. Like the old Rod Stewart albums he’ll cop to owning, the disc has a fast half and a slow half, with the latter borrowing sound textures from the Eagles and Fleetwood Mac, the former echoing pre-hardcore punk (and more Fleetwood Mac, specifically the gonzoid rockers on Tusk). And when he rhymes “I’ve been to college” with “I know what the facts is,” anyone on his wavelength will appreciate the Steve Miller reference.

It all couldn’t be more different from his previous album with the Brett Rosenberg Problem, last year’s Speed Metal from Montreal, which included, among other things, the best love song ever to use the word “douchebag” in its chorus. Drop Dead Air is more of a vintage-model singer-songwriter album, sensitive and otherwise. Rosenberg doesn’t entirely drop his smart-ass sense of humor, but there’s a vulnerable side here too. “Absolutely Not” is a classic example of how to deploy a hook: the chorus makes an emotional point every time it recurs, as the singer keeps getting his hopes up about a potential relationship and then gets shot down anew. It’s the kind of number that’s gotten him a rep as one of the craftier songwriters in town.

Of course, as Rosenberg points out, that and a buck won’t get you on the Green Line. “I think the song itself is losing power,” he suggests over coffee at Bruegger’s. “You try to explain to people the difference between, say, ‘Bridge over Troubled Water’ and ‘Your Body Is a Wonderland’ and they don’t realize that it isn’t the same thing. Even a few years ago, when I was writing worse songs, it seemed easier to get people into them. But I’ve been trying to promote this album on college radio and one program director came back that it was ‘too commercial.’ All I could think was that if I can’t even get on college radio, I’m less commercial than you realize.”

His cynicism accumulated some fuel a couple nights earlier when his other band, the Rudds (for which he plays lead guitar), opened for the Flaming Lips at Bank of America Pavilion. “Every song had the same obvious, ascending pattern. And all that feel-good talk, every song turning into a sing-along, and the guys in Santa Claus costumes dancing on stage — what the hell was that? It sounded like songs that the Beach Boys would have done in 1972, when that guy Jack Rieley [their short-lived manager] was writing all the lyrics. It’s just Odelay syndrome again. People pick the nearest thing that looks a little oddball and convince themselves that it’s the hippest thing that ever came along.”

But he isn’t much more charitable when discussing his own work. His guitar-playing ability? “It’s gotten better since a few years ago, when I wasn’t comfortable on stage and hadn’t replaced that bullshit pseudo Keith Richards sound I had.” His Rumble-finalist set with the Problem in 1994? “An unbearable bar-band set. Everything I don’t like about Mellencamp — all the cheap tricks and obvious rhymes.” The excellent 2002 Shock Twins album, with its Guided by Voices vibe? “It always sounds like them when you get someone with a four-track recorder and no idea what they’re doing.” What about the hopped-up classic-rock sound on the jokingly titled Speed Metal? “I didn’t have anything to say on that record. That was just a Get the Knack kind of album — catchy songs and dirty lyrics, that was the whole idea. That and spending the money we won in the Rumble. We could be a ballsy rock-and-roll band on stage, but I don’t think those records really matter.”

Under prodding, however, he’ll admit that the new disc may be pretty good. You might think he recorded it as a strike for classic pop values, and that’s partly true, but other factors were pressing as well. After five years together, his Problem fell apart when drummer Jason Sloan quit and bassist Geoff Hayton moved to California. After much hemming and hawing, Rosenberg decided to keep the name for his new band: bassist Jim Collins, drummer Richard Adkins, and Ethan Krietzer on keyboards. All appear on the disc, as does local legend David Minehan, but he does most of the work himself.

“I looked around my apartment and said, ‘Okay, here’s a side of me that maybe people haven’t seen.’ I wanted to do something a little honest, and maybe I have something to say about the scene and being a musician in the 21st century. My taste can be pretty flighty, but I think the question is whether the lyrics and the songs stay real. And if you do that kind of record, you’re bound to fall into those typical singer-songwriter themes of being lonely and alienated.”

On the new album he got introspective enough to close with “When I Die,” a song about visiting his grandmother. “She’s doing the things old people do, being hit by pop culture in the most obnoxious way. And I’m thinking that if I feel obsolete as a power-pop songwriter in the 21st century, how does a legally blind 92-year-old feel?” As if on cue, another bad soft-rock hit comes on the Bruegger’s radio, and Rosenberg realizes his mission in life: “It’s hard to be earnest unless you’re John Mayer. So what I really want is to be John Mayer for smart people. Or the Magnetic Fields for idiots.”